Record Information
Version1.0
Creation date2010-04-08 22:04:37 UTC
Update date2019-11-26 02:55:00 UTC
Primary IDFDB000565
Secondary Accession Numbers
  • FDB005752
Chemical Information
FooDB Namealpha-Tocopherol
DescriptionConstituent of many vegetable oils such as soya and sunflower oils. Dietary supplement and nutrient. Nutriceutical with anticancer and antioxidant props. Added to fats and oils to prevent rancidity. The naturally-occurring tocopherol is a single stereoisomer; synthetic forms are a mixture of all eight possible isomers Alpha-tocopherol is traditionally recognized as the most active form of vitamin E in humans, and is a powerful biological antioxidant. alpha-Tocopherol is found in many foods, some of which are custard apple, nopal, bitter gourd, and kumquat.
CAS Number59-02-9
Structure
Thumb
Synonyms
SynonymSource
(+)-alpha-TocopherolChEBI
(2R)-2,5,7,8-Tetramethyl-2-[(4R,8R)-4,8,12-trimethyltridecyl]-3,4-dihydro-2H-1-benzopyran-6-olChEBI
(2R,4'r,8'r)-alpha-TocopherolChEBI
(all-R)-alpha-TocopherolChEBI
5,7,8-TrimethyltocolChEBI
D-alpha-TocopherolChEBI
RRR-alpha-TocopherolChEBI
Vitamin eChEBI
(+)-a-TocopherolGenerator
(+)-Α-tocopherolGenerator
(2R,4'r,8'r)-a-TocopherolGenerator
(2R,4'r,8'r)-Α-tocopherolGenerator
(all-R)-a-TocopherolGenerator
(all-R)-Α-tocopherolGenerator
D-a-TocopherolGenerator
D-Α-tocopherolGenerator
RRR-a-TocopherolGenerator
RRR-Α-tocopherolGenerator
a-TocopherolGenerator
Α-tocopherolGenerator
(R,R,R)-alpha-TocopherolChEBI
(R,R,R)-a-TocopherolGenerator
(R,R,R)-α-TocopherolGenerator
(2R)-3,4-Dihydro-2,5,7,8-tetramethyl-2-[(4R,8R)-4,8,12-trimethyltridecyl]-2H-1-benzopyran-6-olHMDB
a-D-TocopherolHMDB
alpha-delta-TocopherolHMDB
delta-alpha-TocopherolHMDB
DenamoneHMDB
EprolinHMDB
PhytogerminHMDB
PhytogermineHMDB
RRR-alpha-TocopherylHMDB
Vitamin eaHMDB
alpha-TocopherolChEBI
(+)-2R,4'R,8'R-alpha-TocopherolHMDB
(+)-2R,4'R,8'R-α-TocopherolHMDB
(+)-2R,4’R,8’R-α-TocopherolHMDB
(2R,4’R,8’R)-α-TocopherolHMDB
3,4-Dihydro-2,5,7,8-tetramethyl-2-[(4R,8R)-4,8,12-trimethyltridecyl]-(2R)-2H-1-benzopyran-6-olHMDB
alpha-D-TocopherolHMDB
alpha-Vitamin EHMDB
α-D-TocopherolHMDB
α-Vitamin EHMDB
AlmefrolPhytoBank
EmipherolPhytoBank
EtamicanPhytoBank
EvitaminumPhytoBank
ProfecundinPhytoBank
Vitamin EalphaPhytoBank
Vitamin EαPhytoBank
(+)-a-tocopherolbiospider
(+)-alpha-tocopherolbiospider
(+)-α-tocopherolGenerator
(2R,4'R,8'R)-a-Tocopherolbiospider
(2R,4'R,8'R)-alpha-Tocopherolbiospider
(2R,4'R,8'r)-α-tocopherolGenerator
(2R)-3,4-dihydro-2,5,7,8-Tetramethyl-2-[(4R,8R)-4,8,12-trimethyltridecyl]-2H-1-benzopyran-6-olHMDB
(all-r)-a-tocopherolbiospider
(r,r,r)-a-tocopherolbiospider
(r,r,r)-alpha-tocopherolbiospider
(R,R,R)-α-tocopherolGenerator
3,4-Dihydro-2,5,7,8-tetramethyl-2-(4,8,12-trimethyltridecyl)-2H-1-benzopyran-6-ol, 9CIdb_source
a-tocopherolbiospider
Alpha-delta-tocopherolbiospider
Alpha-tocopherolbiospider
Antisterility vitamindb_source
Covitolbiospider
D-alpha-tocopherolbiospider
D-α-tocopherolGenerator
Delta-alpha-tocopherolbiospider
E307db_source
Ephanylbiospider
Ephynaldb_source
Natopherolbiospider
RRR-alpha-tocopherolbiospider
RRR-alpha-tocopherylHMDB
Syntopheroldb_source
Tocopherolbiospider
Vitamin E?db_source
α-tocopherolGenerator
Predicted Properties
PropertyValueSource
Water Solubility7.0e-06 g/LALOGPS
logP8.84ALOGPS
logP10.51ChemAxon
logS-7.8ALOGPS
pKa (Strongest Acidic)10.8ChemAxon
pKa (Strongest Basic)-4.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area29.46 ŲChemAxon
Rotatable Bond Count12ChemAxon
Refractivity135.37 m³·mol⁻¹ChemAxon
Polarizability55.29 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC29H50O2
IUPAC name(2R)-2,5,7,8-tetramethyl-2-[(4R,8R)-4,8,12-trimethyltridecyl]-3,4-dihydro-2H-1-benzopyran-6-ol
InChI IdentifierInChI=1S/C29H50O2/c1-20(2)12-9-13-21(3)14-10-15-22(4)16-11-18-29(8)19-17-26-25(7)27(30)23(5)24(6)28(26)31-29/h20-22,30H,9-19H2,1-8H3/t21-,22-,29-/m1/s1
InChI KeyGVJHHUAWPYXKBD-IEOSBIPESA-N
Isomeric SMILESCC(C)CCC[C@@H](C)CCC[C@@H](C)CCC[C@]1(C)CCC2=C(O1)C(C)=C(C)C(O)=C2C
Average Molecular Weight430.7061
Monoisotopic Molecular Weight430.381080844
Classification
Description Belongs to the class of organic compounds known as tocopherols. These are vitamin E derivatives containing a saturated trimethyltridecyl chain attached to the carbon C6 atom of a benzopyran ring system. The differ from tocotrienols that contain an unsaturated trimethyltrideca-3,7,11-trien-1-yl chain.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassQuinone and hydroquinone lipids
Direct ParentTocopherols
Alternative Parents
Substituents
  • Tocopherol
  • Diterpenoid
  • 1-benzopyran
  • Benzopyran
  • Chromane
  • Alkyl aryl ether
  • Benzenoid
  • Oxacycle
  • Organoheterocyclic compound
  • Ether
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Physiological effect

Health effect:

Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Biological role:

Industrial application:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateLiquid
Physical DescriptionNot Available
Mass CompositionC 80.87%; H 11.70%; O 7.43%DFC
Melting PointMp 2.5-3.5°DFC
Boiling PointBp0.03 140°DFC
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]25D +0.65 (EtOH)DFC
Spectroscopic UV Data[neutral] lmax 292 () (EtOH) (Berdy)DFC
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-0159-2900500000-03e8a824731610752eb32014-09-20View Spectrum
GC-MSalpha-Tocopherol, 1 TMS, GC-MS Spectrumsplash10-000i-1390000000-fc8c4f9b9405598ede7fSpectrum
GC-MSalpha-Tocopherol, 1 TMS, GC-MS Spectrumsplash10-00dr-9150010000-c4abc0e689e9b2476b9dSpectrum
GC-MSalpha-Tocopherol, 1 TMS, GC-MS Spectrumsplash10-0f79-1190040000-663296a69129a59be1a6Spectrum
GC-MSalpha-Tocopherol, non-derivatized, GC-MS Spectrumsplash10-000i-1390000000-fc8c4f9b9405598ede7fSpectrum
GC-MSalpha-Tocopherol, non-derivatized, GC-MS Spectrumsplash10-00dr-9150010000-c4abc0e689e9b2476b9dSpectrum
GC-MSalpha-Tocopherol, non-derivatized, GC-MS Spectrumsplash10-0f79-1190040000-663296a69129a59be1a6Spectrum
Predicted GC-MSalpha-Tocopherol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0aor-9886300000-b3225facac6ebdd8ddbdSpectrum
Predicted GC-MSalpha-Tocopherol, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-000l-7735900000-1585eb83c1211ebe95f2Spectrum
Predicted GC-MSalpha-Tocopherol, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSalpha-Tocopherol, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-03di-9600100000-aaf885290800a10d3fb22012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-01wr-9300000000-f0c814976a58a9d837ca2012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0f79-1494700000-6b5f8f817c5a5429ed702012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - EI-EBEB (JMS-HX/HX 110A, JEOL) , Positivesplash10-00lr-4910600000-1eda05dacf9642d7cea02012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-014i-0900000000-a5860634bfd1ceb6833f2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-0159-0900500000-5a3bc17152cb61859b2c2021-09-20View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0842900000-f51286676592fd1841932017-07-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-1920000000-1994f86bec2bb4a77b9c2017-07-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-066r-3930000000-02190bf16d5d85d44bce2017-07-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0110900000-c3541294fc60a7a8cc7e2017-07-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01t9-0730900000-553c4898757f6876036c2017-07-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-03e9-0920200000-276273a531fed5b3a2b02017-07-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-3013900000-4985082235edff7c4b8c2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05r1-9313200000-cbc230d5dd20c629ffab2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9320000000-5958d2e1d5b687b012c12021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0000900000-d3ddef81c134412455e12021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-0310900000-30597e14cf876e4e47642021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-08g0-2982400000-371737325df4dbb523b22021-09-22View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 500 MHz, CDCl3, experimental)Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, CDCl3, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 25.16 MHz, CDCl3, experimental)Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, CDCl3, experimental)Spectrum
ChemSpider ID14265
ChEMBL IDCHEMBL47
KEGG Compound IDC02477
Pubchem Compound ID14985
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDDB00163
HMDB IDHMDB01893
CRC / DFC (Dictionary of Food Compounds) IDBDR14-R:BDR14-R
EAFUS IDNot Available
Dr. Duke IDALPHA-TOCOPHEROL
BIGG ID2296507
KNApSAcK IDC00007366
HET IDVIV
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDAlpha-Tocopherol
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
Anti-Alzheimeran52217 An agent that inhibits the progression of Alzheimer's disease, reducing beta-amyloid plaque formation and neuroinflammation. Therapeutically, it improves cognitive function and memory, commonly used in managing mild to moderate Alzheimer's disease and other neurodegenerative disorders.DUKE
Anti anginal52217 An agent that reduces angina symptoms by improving blood flow to the heart, commonly used in managing angina pectoris, coronary artery disease, and other cardiovascular conditions, to alleviate chest pain and prevent cardiac complications.DUKE
Anti-arthritic52217 An agent that reduces joint inflammation and alleviates symptoms of arthritis, commonly used in managing rheumatoid arthritis, osteoarthritis, and other inflammatory joint disorders, to improve mobility and quality of life.DUKE
Anti-asthmatic49167 An agent that relieves bronchospasm and inflammation, commonly used to manage asthma symptoms, chronic obstructive pulmonary disease (COPD), and other respiratory disorders, improving lung function and overall respiratory health.DUKE
Anti-atherosclerotic38070 An agent that prevents or slows the formation of atherosclerosis, a condition characterized by plaque buildup in arteries. It reduces inflammation, improves lipid profiles, and inhibits platelet aggregation, commonly used to manage cardiovascular diseases, such as coronary artery disease, and prevent heart attacks and strokes.DUKE
Anti-cancer35610 An agent that inhibits the growth and proliferation of cancer cells, used to treat and manage various types of cancer, including chemotherapy, targeted therapy, and immunotherapy, to reduce tumor size, prevent metastasis, and improve patient survival.DUKE
Anti-cataract52217 An agent that prevents or slows the formation of cataracts, reducing oxidative stress and inflammation in the lens of the eye, commonly used to manage age-related cataracts and other ocular disorders.DUKE
Anti convulsant52217 An agent that reduces or prevents seizures, commonly used in managing epilepsy, neuropathic pain, and mood disorders, by stabilizing abnormal electrical activity in the brain.DUKE
Anti-dementia52217 An agent that slows or prevents cognitive decline, reducing symptoms of dementia. It plays a biological role in neuroprotection, enhancing neuronal function and survival. Therapeutically, it is used to manage Alzheimer's disease, vascular dementia, and other neurodegenerative disorders, improving memory, cognition, and daily functioning.DUKE
Anti-diabetic52217 An agent that regulates blood sugar levels, enhancing insulin sensitivity or secretion. Therapeutically, it's used to manage diabetes, reducing symptoms and complications, and commonly prescribed to treat type 1 and 2 diabetes, as well as gestational diabetes.DUKE
Anti-infarctal52217 An agent that reduces myocardial infarct size, protecting against cardiac damage. It plays a biological role in inhibiting apoptosis and inflammation, promoting therapeutic applications in cardiovascular disease management, and is used to treat conditions such as myocardial infarction, heart failure, and cardiac arrhythmias.DUKE
Anti-infertility52217 An agent that enhances reproductive health, promoting fertility and conception. Its biological role involves regulating hormonal balance and improving reproductive function. Therapeutically, it is used to treat infertility disorders, with key medical applications in assisted reproduction, polycystic ovary syndrome (PCOS), and unexplained infertility.DUKE
Anti-ischemic52217 An agent that reduces or prevents tissue damage from inadequate blood flow, commonly used to manage angina, heart attacks, and strokes by improving oxygen delivery and reducing cardiac workload.DUKE
Anti-maculiticAn agent that reduces macular inflammation, commonly used in managing age-related macular degeneration and diabetic macular edema, promoting vision preservation and reducing disease progression.DUKE
Anti-mutagenicAn agent that interferes with the mutagenicity of a substance, preventing DNA damage and mutations. Its biological role is to protect cells from genetic alterations, and it has therapeutic applications in cancer prevention and treatment, as well as key medical uses in reducing the risk of genetic disorders and birth defects.DUKE
Anti neuropathicAn agent that relieves symptoms such as pain, numbness, and tingling caused by damage or disease affecting the somatosensory nervous system, commonly used in managing conditions like diabetes, shingles, and nerve injuries.DUKE
Anti-oxidant22586 An agent that neutralizes free radicals, reducing oxidative stress and cell damage. Its biological role involves protecting cells from harm, and it has therapeutic applications in managing chronic diseases, such as cancer, diabetes, and neurodegenerative disorders, with key medical uses including anti-aging, anti-inflammatory, and cardio protective effects.DUKE
Anti-Parkinsonian48407 An agent that alleviates symptoms of Parkinson's disease, enhancing dopamine levels and improving motor function, commonly used to manage tremors, rigidity, and bradykinesia in neurodegenerative disorders.DUKE
Anti radicularAn agent that relieves inflammation or irritation of the nerve root of a tooth, reducing pain and discomfort. Its biological role is to target and alleviate radicular pain, with therapeutic applications in endodontics and key medical uses in root canal treatments and tooth sensitivity management.DUKE
Anti-retinoticAn agent that inhibits retinoic acid activity, acting as a receptor antagonist. It plays a biological role in regulating cell growth and differentiation. Therapeutically, it has applications in managing retinoic acid-related disorders, with key medical uses including treatment of retinoic acid toxicity and certain types of cancer.DUKE
Anti-rheumatic52217 An agent that reduces inflammation and alleviates symptoms of rheumatic diseases, such as arthritis. It plays a biological role in modulating the immune system and inhibiting pro-inflammatory pathways. Therapeutically, anti-rheumatics are used to manage conditions like rheumatoid arthritis, lupus, and osteoarthritis, reducing pain, swelling, and joint damage. Key medical uses include slowing disease progression and improving quality of life for patients with chronic rheumatic conditions.DUKE
Anti-stroke52217 An agent that prevents or reduces the severity of stroke, typically by inhibiting blood clot formation or improving cerebral blood flow, commonly used in managing cardiovascular diseases, preventing stroke recurrence, and reducing stroke-related brain damage.DUKE
Antitumor35610 An agent that inhibits tumor growth and proliferation, playing a crucial role in cancer treatment. Therapeutically, antitumors are used to manage various types of cancer, including chemotherapy, targeted therapy, and immunotherapy, helping to reduce tumor size, prevent metastasis, and improve patient outcomes.DUKE
Antitumor promoter35610 An agent that inhibits tumor growth and progression, reducing cancer cell proliferation. Therapeutically, it prevents tumor development and spread, with key medical uses in cancer prevention and treatment, particularly in combating carcinogenesis and metastasis.DUKE
Cancer preventive35610 An agent that inhibits the development and progression of cancer, reducing tumor formation and growth. It plays a biological role in blocking carcinogenic pathways, and has therapeutic applications in chemoprevention. Key medical uses include reducing the risk of cancer in high-risk individuals and preventing cancer recurrence.DUKE
Cardioprotective38070 An agent that protects the heart from damage, reducing the risk of cardiovascular disease. It plays a biological role in mitigating cardiac stress and injury, with therapeutic applications in preventing heart attacks, strokes, and arrhythmias, and key medical uses in treating hypertension, heart failure, and coronary artery disease.DUKE
CirculotonicA cardiac stimulant that enhances cardiovascular function, increasing cardiac output and blood pressure. Therapeutically, it's used to treat hypotension, shock, and heart failure, improving circulation and overall cardiovascular health. Key medical uses include managing cardiogenic shock, post-operative hypotension, and severe dehydration.DUKE
Immunomodulator50846 An agent that regulates the immune system, modifying its response to maintain balance. Therapeutically, it's used to treat autoimmune diseases, prevent transplant rejection, and manage chronic inflammatory conditions, such as rheumatoid arthritis and multiple sclerosis.DUKE
Enzymes
NameGene NameUniProt ID
Nuclear receptor subfamily 1 group I member 2NR1I2O75469
Glutamate--cysteine ligase catalytic subunitGCLCP48506
Glutathione S-transferase Mu 3GSTM3P21266
Glutathione S-transferase omega-1GSTO1P78417
Glutathione S-transferase A2GSTA2P09210
Glutathione S-transferase PGSTP1P09211
Serine palmitoyltransferase 1SPTLC1O15269
Alpha-tocopherol transfer proteinTTPAP49638
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Saxholt, E., et al. 'Danish food composition databank, revision 7.' Department of Nutrition, National Food Institute, Technical University of Denmark (2008).
— U.S. Department of Agriculture, Agricultural Research Service. 2008. USDA National Nutrient Database for Standard Reference, Release 21. Nutrient Data Laboratory Home Page.
— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.